Dimethoxyethane

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Not to be confused with dimethoxymethane.
Dimethoxyethane
Dimethoxyethane
Identifiers
CAS number 110-71-4 YesY
ChemSpider 13854808 YesY
ChEBI CHEBI:42263 N
RTECS number KI1451000
Jmol-3D images Image 1
Properties
Molecular formula C4H10O2
Molar mass 90.12 g mol−1
Appearance Colorless liquid
Density 0.8683 g/cm3
Melting point −58 °C (−72 °F; 215 K)
Boiling point 85 °C (185 °F; 358 K)
Solubility in water miscible
Hazards
EU classification Flammable (F)
Toxic (T)
Repr. Cat. 2
R-phrases R60, R61, R11, R19, R20
S-phrases S53, S45
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point −2 °C (28 °F; 271 K)
Related compounds
Related Ethers Dimethoxymethane
Related compounds Ethylene glycol
1,4-Dioxane
Diethylene glycol dimethyl ether
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Dimethoxyethane, also known as glyme, monoglyme, dimethyl glycol, ethylene glycol dimethyl ether, dimethyl cellosolve, and DME, is a clear, colorless, aprotic, and liquid ether that is used as a solvent, especially in batteries.[1] Dimethoxyethane is miscible with water.

The lowest energy form of dimethoxyethane in the gas phase is the gauche, rather than the anti conformer.

Production[edit]

Monoglyme may be manufactured by a number of methods:[2]

2 CH3OCH2CH2OH + 2 Na → 2 CH3OCH2CH2ONa + H2
CH3OCH2CH2ONa + CH3Cl → CH3OCH2CH2OCH3 + NaCl
CH3OCH3 + CH2CH2O → CH3OCH2CH2OCH3

Applications as solvent and ligand[edit]

Together with a high-permittivity solvents (e.g. propylene carbonate), dimethoxyethane is used as the low-viscosity component of the solvent for electrolytes of lithium batteries. In the laboratory, DME is used as a coordinating solvent.

Dimethoxyethane is often used as a higher boiling alternative to diethyl ether and THF. Dimethoxyethane forms chelate complexes with cations and acts as a bidentate ligand. It is therefore often used in organometallic chemistry like Grignard reactions, hydride reductions, and palladium-catalyzed reactions like Suzuki reactions and Stille couplings. Dimethoxyethane is also a good solvent for oligo- and polysaccharides.

References[edit]

  1. ^ D. Berndt, D. Spahrbier, "Batteries" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_343
  2. ^ Dimethoxyethane

External links[edit]